Chenopodolans E and F, two new furopyrans produced by Phoma chenopodiicola and absolute configuration determination of chenopodolan B. Issue 51 (22nd December 2016)

• Record Type: Journal Article
• Authors: Evidente, Marco; Cimmino, Alessio; Zonno, Maria Chiara; Masi, Marco; Santoro, Ernesto; Vergura, Stefania; Berestetskiy, Alexander; Superchi, Stefano; Vurro, Maurizio; Evidente, Antonio
• Is Part Of: Tetrahedron. Volume 72:Issue 51(2016)
• Page Start: 8502
• Page End: 8507
• Publication Date: 2016-12-22
• Subjects: Chenopodium album -- Phoma chenopodiicola -- Phytotoxic furopyrans -- Chenopodolans E and F -- Absolute configuration -- Chiroptical spectroscopy -- DFT calculations; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.11.024
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Two new furopyrans, named chenopodolans E and F (1 and 2 ), were isolated from the liquid culture of Phoma chenopodiicola, a fungal pathogen proposed for the biological control of Chenopodium album, a common worldwide weed of arable crops. They were characterized using spectroscopic methods as 3-(3-methoxy-2, 6-dimethyl-7a H -furo[2, 3 b ]pyran-4-yl)-but-2-enoic acid methyl ester and 1-(3-methoxy-2, 6-dimethyl-7a H -furo[2, 3 b ]pyran-4-yl)-ethanone, respectively. Furthermore, the absolute configuration of chenopodolan B (3 ) was established to be (7a R, 9 S ) by a combined application of the advanced Mosher's method and of quantum mechanical calculations of chiroptical (ECD and ORD) properties. When 1 and 2 were assayed on punctured leaves at 2 μg/μL, only 2 was active on Sonchus arvensis while 1 caused around 75% larval mortality on Artemia salina larvae at 0.1 μg/μL. Graphical abstract: